Lucky Tales Pt. 02: Gloryhole Gals

Author's note: This is the second in a series of (generally) shorter stories about the couple in the Lucky Over 40 series, and their friends. They have a rather adventurous sexual relationship, and are very much in love. Overall, these tales are about them exploring various sexual kinks. You do not have to read any of that series to enjoy this, although some things might be better understood if you do.

Please check the story Tags to see what you may or may not like. There is also reluctance, some cock worship, a prostate massage, and a cum kiss. If anything bothers you, it might be best to try another story, otherwise, I hope you enjoy reading this one. If you like it, please add some stars, and even a comment at the end. Your feedback does help inspire me to continue writing.

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Jill and I have been having a lot of fun sexually "exploring," by trying different things. It all started about a month after we began dating, and took off like a rocket from there. I feel like the luckiest guy in the world to be with her. We also have a pretty unusual relationship in that Jill occasionally "lends my services" to friends, like JJ, in order to ease their sexual frustrations. JJ has become a good friend to us both ever since we met her, when I took Jill to JJ's Adult Toy Store on a special kind of date. We call her JJ because her name is also Jill, and though that's part of why the girls bonded, it also got confusing, especially in certain situations.

On the drive to JJ's store I told Jill some of what happened earlier this week. "So, I sent Ron to JJ's store to look for bachelor party stuff while they were on standby with the Ambulance the other day. He was working with Donna, who thought it was pretty fun. She did some browsing of her own while JJ showed Ron around and suggested some stuff. But they got an Ambulance call and had to run before buying anything -- apparently Donna had already made some purchases, though. They stopped back a few hours later and found JJ had picked out a bunch of things for Ron so he just bought the lot; putting it on my tab!" Jill laughed at that part.

"Yeah, I'll get some of it back when others chip in, maybe. Either way, it's worth it to me. I asked him if she was helpful and he said 'very much.' I told him Jill's really nice, and he agreed. I said she's really attractive, too, and he called her 'hot.'"

"I bet he did, `cause she is! She gets you going," Jill added, grinning.

I laughed, "Yeah, well bottom line is, I convinced him to ask her out on a date -- after I checked to see if JJ'd be interested, of course. I called her just to say 'Did my guy come over, and did you help him out?' kind of thing. She said something like 'I'm always happy to help a man in uniform, especially a hunky one.' And yup, she's interested."

"Yeah, I know all about her side of it. We talked already."

"I should have known. They were supposed to have a date last night, you know about that I assume."

"Of course, she told me this morning. They had a nice casual time, but really hit it off. She gave him a goodnight kiss, and wanted to jump his bones, but decided it would be better to hold off and go for the long game instead of a one night stand. She's supposed to see him again soon."

"Yeah, she sure is. Ron's looking forward to another date, too. I think I did Ok, so far..."

"Yeah, good for you!" she said, squeezing my hand. "What about your little gloryhole escapade, with a blowjob for the guy getting married..."

"Less," I sort of interrupted.

"Yeah, him, getting one last anonymous blowjob...from Ruth, right? And Ron getting one from JJ, but not knowing it's her. Still planning on trying that?"

"We sure are. JJ's gonna see him -- or a part of him -- tonight, in just a little while. And we're gonna help, sort of. That's why we're headed there now."

"What, really? Does JJ know? I think she would've told me..."

"Yeah, she knows. Look, I've played along with your plans several times, and now I need you to play along with mine tonight. Will you do that? For this to work right I need your full cooperation, Ok?"

"Um, yeah, Rob, sure," she said, a bit confused, or maybe concerned, or both.

"Hey, you trust me right?"

"Of course."

"Good. Just follow my lead and do what I need you to at the store, like I do for you on your adventures. Then this'll all work out, just like yours do, Ok?"

"Yeah, Ok," she smiled at me and squeezed my hand again. "I'm not sure what's really going on, or what we're supposed to do, but I trust you and I'll do what you need, for JJ."

"Great. If you play along like I tell you to, I think you'll really enjoy it."

"Ok, Tiger, whatever you say."

When we got to the store JJ saw us as soon as we walked in, waving for us to follow her down the hallway to the video rooms with the gloryholes. "They may be here any minute and I wanna be sure they don't see any of us." She ushered us into the larger room, number 3, and closed the door behind us.

JJ gave us each a hug and kiss, then said to me, "Thanks for doing your little set-up thing the other day. We had fun last night, and I hope we both do today, too, even if he doesn't know it's us, I mean me. This is a little weird, maybe, but hopefully he won't think it was too weird when he finds out later. Shit, suddenly I'm nervous."

"If you do a good job, I'm sure he'll be very happy. I told him you have a pretty strict rule about not doing customers, so..."

"Um, sorta strict, considering technically you're a customer, and so is he."

"The point is he shouldn't suspect it's you until you tell him, if and when you want to. Anyway, are you ready to meet little Ron..."

"Cute. Yeah, I'm ready. But he may not be all that little -- just like little Robbie," she laughed.

"Hey what about Less? Where's Ruth, or whoever is taking care of him? Are they using another room? And why do we need to be here?" Jill was full of more questions than usual.

"Relax, it's under control. I know you like watching, and you'll like this. Just do what I say, remember?"

JJ winked at me, then turned to Jill, "I dunno what all he has up his sleeve, but just do what he says, don't ask so many questions, and don't mess this up for me, please?"

"Yeah, Ok," Jill replied, still sounding unsure.

Just then we heard someone enter the room next-door, followed by the one on the other side. "Alright ladies, places, it's almost show time," I said quietly. "Jill, you're going to do Less while JJ sucks Ron. You've told JJ you still want to try the gloryhole."

"What?" she said, looking shocked.

"You also said you'd like to get spit-roasted sometime, so if you do a good job on him, I'm gonna fuck you from behind while you finish him off. So drop your shorts and kneel down over there, right now!"

"Um, I'm not sure about this... But I'll try it... for JJ," she giggled, taking off her shorts and undies. "Wait, how do we know who's who?"

"Deejay's out front and directed them back here, with Ron in number 2 and your guy in 4. She's supposed to tell them to use the little doors instead of the round holes, so we get better access."

Just as she said that, one door in the wall opened and a stiff cock emerged near Jill's face. Soon after, the same thing happened on the other wall.

The girls knelt down and started to stroke the cocks, when the door to our room suddenly opened, startling us all. Deejay stepped in, saying "Hi!" a bit too loudly, then whispered "I had to come down to check. Ooo, I see, you've got a nice grip on Ron, and Less is in good hands with Jill," she tittered.

With that confirmation, JJ kissed the purple head in front of her, gave it a long lick, then wrapped her lips around it. Jill watched her a moment, looked back at the thick cock she was holding, let out a deep breath, and did the same.

"So who's minding the store?" I asked Deejay.

"Oh, Teddy is. He knew how interested I was and finally told me I could go down and check it out. Or whatever..."

"Whatever?" I asked.

"Well, he knows Jill, um... sorta got stage fright when she tried this on him, and wondered if it might happen again. He thought I should be a good friend and back her up. Just in case, you know?"

"That was his idea?"

"Well, I may have suggested it first, but he's Ok with it. Really, he is! He's not the jealous type, and he doesn't need to be `cause he's got me hooked. Kinda like you and Jill, I guess. Oh, man, look at her. I think she's getting into it this time."

She was, from the look of it. She was sliding her mouth up and down a good sized cock, slurping and humming "mmm...mmm," as she went. She had a hand through the opening cupping his balls, and one between her own legs.

"Yup, she's doing very well, so I've got a bonus for her," I said, pulling my shorts off.

"Mmm, more like a boner," Deejay said, ogling my partial erection. "But if you're gonna stick that gorgeous cock someplace you should get it really hard first. Let me help with that." Taking hold of my dick, she dropped down and filled her mouth.

"Deejay!" I stammered. "Umm, Ok, sure... Fuck, you've gotten better at that."

"I had a good teacher, remember," she said, pulling her moth off me with a slurp. "And some tips from Jill," she added, with a big lick up the underside of my shaft. "Plus some practice time with my Teddy-the-Bear." She took me back in her mouth and noisily bobbed her head along nearly the whole length of my fully stiff cock, gagging slightly when she got to the bottom. Her hands held my ass tightly, fingers in my butt crack. I don't know if she did that to purposely excite me more, but it did...

"Ok, professor, I think he's good to go now," she said after pulling her mouth off, and wiping it with her hand. "I like sucking you, almost as much as I like you eating me. Maybe you'll return this favor, soon?" she smiled as she sat on the upholstered bench seat.

"Um, yeah, I'd like that. We'll see," I said as I moved over to Jill and reached my hand between her legs from behind. She was rubbing herself, and pulled her hand away with a moan as my fingers slid through her lips and inside. She took her mouth off the thick cock and licked its head before stroking it. Looking back over her shoulder at me she asked, "Am I doing a good job, boss? Good enough for that bonus you promised?" She kissed and licked the cock several times as she kept stroking. I could hear Less moaning softly.

"Yeah, I think maybe so. You finish him off and I'll see what I can do to finish you." My fingers found her g-spot and stroked it, while I rubbed my dick on her ass. She wiggled her bottom back at me, and her pussy squeezed my fingers. She sucked hard on his cock, making sloppy, slurppy sounds.

After a minute she popped her mouth off the dick and whispered to me, "Fuck me, now, please!" She blew me a kiss and returned to fervently sucking Less.

I slid my finger from her sopping snatch and she moaned a little, the cock still in her mouth. I positioned myself and rubbed my cock head on her wet pussy lips. She moaned again and pushed back onto me. I slid into her fully, with barely any resistance. Her cunt soon gripped me and her pelvis gyrated on my stick. She moaned louder, sucked harder, and Less exclaimed "Yeah... Oh yeah!"

I pumped my rigid, throbbing cock in and out of her eager pussy. Damn, she always feels so good. A couple times we got out of sync and I slid all the way out, but it slipped right back in her warm, wet sex all on its own. She rocked back and forth, helping my cock move in her cunny as her mouth moved along the thick prick. She moaned and hummed with pleasure, the vibrations obviously pleasing less as well.

While fucking Jill, I glanced across the room. I heard JJ uttering cute little sounds as she devoured the cock sticking through the hole in the wall. Her hand was in the hole, but I couldn't see what it was doing. She seemed very happy, and judging by how the cock kept pushing forward, like its owner was trying to climb through the small opening dick first, I'm sure Ron was fully enjoying it, too.

I noticed another, almost plaintive, sound and looked over to see Deejay with her hand in her open pants, and the other inside her shirt. Our eyes met and she smiled coyly, tucking her head down. "This is hot. I like seeing you two having fun like this. I wish Teddy was here, with his head between my legs...or his cock in me. Mmmm...oh, I'm gonna...mmm...come..." She closed her eyes and tipped her head back.

I began to pound Jill faster, my thighs slapping against her bottom. When I saw I was pushing her too hard into the cock poking through the wall I backed off. It was just in time to hear a low growl from the other room, "Urrgghhh, fuuuck." Jill's head lurched; she grunted slightly and stopped rocking. Several seconds later she released the cock from her mouth, licking the tip before it retreated through the wall. The little door closed a moment later.

Jill wiped her mouth with her hand and sighed, pulling off me with another sigh. She turned and sat on the floor, leaning against the wall. "Fuck, he gave me a mouthful. Not bad, but not nearly as good as you. Maybe he should try pineapple juice," she laughed.

"We could give them a case of it for a wedding present," I chuckled.

"Oh, damn, that was kinda fun, Tiger. Thanks for making me do it. But, my jaw's tired after that fat cock. One of the many reasons I prefer your perfect penis," she said with a big smile and a wink. "We didn't finish our part, though, sorry. You wanna finish now, or wait `till later?"

"Um, well, I think I can wait a bit," I said, my cock still quite erect and oozing pre-cum.

"Hmm, you need a little clean-up there, Babe. Let me lick it off for you." Crawling in front of me, she cleaned my cock head without using her hands. She giggled when it bobbed around as she licked. I was still pretty hard and she teased, "I don't know if he can wait until we get home..."

Just then we heard JJ getting louder, making sensual sounds, and almost sticking her head through the hole in the wall. She had a hand between his legs, pulling as she pushed her mouth fully onto his cock. Deep moaning came from the other room, and JJ began sort of gulping. "I think Ron just finished," Jill whispered.

After several strokes with her mouth, JJ let the cock slip out; giving the tip a couple licks, followed by a nice tender kiss. We heard a soft "Thank you" through the wall. Jill and I looked at each other and smiled, but Deejay didn't catch it and asked "What?"

Before we could answer, JJ replied, in a soft southern belle sort of drawl, "Naw, thank you, darlin'," as the cock backed out of sight and the little door closed. She turned and sat on the floor, slumping against the wall. A muffled voice was heard in the hall and the door next to ours shut, as Jill and I broke out laughing.

"What? Never seen a satisfied woman after a good blow job?"

"No, never heard your southern accent, darlin'," Jill said, in her own Scarlet O'Hara voice.

"Oh that. I just didn't want him to recognize my voice, but I really wanted to thank him, `cause I really enjoyed that. But I wanna see if he likes pineapple juice..." she mused. "So hey, how was yours Jilly? I wasn't really watching you guys. Was it good? Did Rob spit-roast you? And Deejay, why are you still here? Who's out front?"

"Who's fulla questions now? You two are almost sisters, I swear. She can tell you the details, but when she finished him off, she did the exact same slump against the wall as you. That's what I was laughing at." Jill bit her lower lip and swatted my ass. That made me lurch, which caused my erection to bob and sway.

"Damn I like seeing that cock," JJ said, "And it's still looking for action. Did he finish with you, Jilly?"

"Um, no. He said he'd wait `till later, but I'm not sure the poor thing will make it."

"I'll volunteer to take care of it, if you want," Deejay offered eagerly. "I mean, you both just had a workout with your mouths and all..."

"Hey, didn't I see you blowing him before he climbed over behind Jill?" JJ chided.

"Oh? What was that about?" Jill inquired, I'm not sure of whom.

"Well, he wasn't hard enough, so I was just helping out. You know... His cock looked so good, and it's so suckable, and..."

"Yeah, Ok, I can't argue with that. I guess you're off the hook. But you've got your own stud muffin waiting out front," Jill told her.

"Stud muffin?" I snickered to myself.

"Hey, you're my big sexy stud muffin," she said hugging me and squeezing my butt cheeks with both hands. "And I love this muffin part," she added, with another squeeze.

"Deejay, go out front and tell Teddy that when I come back -- in a bit -- you two can come in here and have some private time to...take care of things," JJ told her.

"But, you said we weren't supposed to fool around back here during work..."

"Hey, who's the boss? I can make and break...or bend," JJ added looking at me, "the rules as I see fit. I think you love-birds might be overly distracted right now and need to take care of something so you can concentrate on work for the rest of the night."

"Um, yeah, Ok boss. And, THANKS!" Deejay responded, bolting out the door.

"So, stud, who's gonna take care of you? And Jill honey, do you need some relief for yourself? I know I do after that beautiful cock being only in my mouth. Oh, and 'little Ron' isn't very little. He's damn close to your size, stud, maybe a little thinner, with a cute little curve. He's got a nice large head I loved locking my lips on and swirling my tongue around. Ooo, I should order another one of those cock molding kits..."

"Ha, I bet he'll appreciate that..." I chuckled.

"It's not for his benefit, silly," JJ laughed. "But I'll make it worth his while, just like I need to do for you -- with Jill's permission of course."

"We'll see, JJ," Jill told her. "You may have your own stud muffin now."

"Mmm, I haven't seen his muffin yet, but it felt nice tonight. He seemed to like my caresses, but I didn't try fingering him. I wonder when he'll let me probe his p-spot? Or use my Feeldoe..."

"Don't rush it!" I told her. "You can probably win him over, hot stuff; you're very talented. Just take it easy, as I'm sure you know, even though you seem to have a hard time holding back."

"Yeah, well... So, Jill, what're we gonna do about this hot stud, and about satisfying our needs, too?"

"I have a feeling you've got something in mind. And since you're the sex therapist-gonna-be, I wanna hear it."

"Well, I think at least one of us oughta get a good fucking, and the other could make use of his talented tongue."

I smiled and raised my eyebrows, looking at Jill to see her opinion. She smiled at me and replied, "Yeah that works... for starters anyway. I call heads -- his head, the smaller one I mean. Shit, that metaphor is pretty confusing. I wanna get fucked and he can eat you. What's the best way to do that, JJ?"

"Well, there are options, but without getting into some gymnastics from the Kamasutra, it's easiest to just have him lie down while you go cowgirl and I sit on his face."

"That sounds good, but it's hard for me to concentrate on either one of you with the other being such a big distraction. How about I fuck Jill, and then I'll eat JJ while Jill watches. You like that, don't you?"

"Mmm, yeah, I'm Ok with that, if you can wait a bit, JJ?"

"Yeah, I can do some warm ups while I wait my turn," she laughed.

"Ok, then. Kneel on the bench, Babe, hands on the back, and spread those nice long legs for me." When she did, I could see her pubes glistening with her arousal. I ran my fingers between her legs, across her moist pussy and up her butt crack, while stroking my growing cock. Jill eyed me over her shoulder, and JJ watched from the other end of the cushioned bench.